Tag: Stream of Consciousnesses

Categories
Reading

Day 273 and The Newsstand

I used to travel a lot. It seems like another life, but before the pandemic airports were my most important liminal space. Even as a child this was true as my father loved taking us on trips. That emotional weight meant the airport have always had significance to me. This persistent exposure to airports lead to me to developing certain affinities and aversions in my routines around travel. But the one that I liked the most was buying something at the newsstand.

There was a period as a teenager where I thought carrying both the The Economist and Rolling Stone (neither of which I read anymore) was just the height of intellectual signaling. And no place was more crucial to signal than inside an airport. I could meet someone in passing that would change my life and they needed to see immediately that I was both smart and cultured. Yes it’s embarrassing now.

But this signaling was part of a wider ritual I felt was important to ground myself. Even if I felt the unsteadiness of traveling, I could bring routine and ritual into it. I knew no matter how much I anxiety or uncertainty I felt around a given trip I could always treat myself to buying something to read from the airport newsstand.

Generally I would pick up some kind of periodical. I’d leave myself time to browse the newsstands for at least ten minutes so I could adequately cover all the weird genres. Because I grew up in a small town and not a proper city, the only newsstand I ever encountered was at the airport. There was simply no place that held as many magazines covering as many topics.

And while I had the Internet very early in my life, the actual transition away from physical publishing wasn’t as far along. It’s not that I loved magazines so much as it was the only place I could find writing that wasn’t a novel was in newsstand. Now of course I read blogs, email newsletters, forums, Subreddits and my beloved Twitter. But the memories I have of finding new worlds came from newsstands. And while I may have literally been going someplace new, it was never quite as horizon broadening as picking out what I was going to read.

Categories
Internet Culture Reading

Day 271 and Correspondence

I love writing to others. I had some pen pals as a child but it wasn’t until as a teenager that the Internet gave me the chance to correspond with practically whomever I liked. And it’s been one of the great joys of my life to reach out to others for conversation.

I developed a habit of writing to journalists, authors and academics whose work I admired. Many of them maintained email addresses and personal websites even back before social media. If you are ever worried that someone will find it odd or unsettling to receive a note from you, don’t fret. I can share that if you are polite and sincere outreach is almost universally appreciated. Most people want to be seen. If you feel you’ve seen someone then you should share it with them. It’s a kindness to you both.

While I particularly like short form correspondence like Twitter, there is no substitute for a more in-depth and layered letter. I’m personally a fan of the threaded twenty response deep email chain. I think of it as like the letter writing of our forefathers. Maybe it’s a bit less satisfying to our heirs than discovering a box of letters but I’ve got a fantasy that the Ken Burns of the future will make excellent use of email and chat logs.

If you aren’t convinced of the benefits of reaching out through writing feel free to test it out on my before you write a letter to your favorite author or thinker. We just might become pen pals.

Categories
Finance Startups

Day 270 and The Circle of Capital

Capital has evolved a lot in my life. The dynamics have changed so much in the 30 years I’ve been ambiently around venture it’s barely the same business. And yes I mean since I was a kid. The apocryphal family history is that I was born on the poor side of Silicon Valley while my unemployed father was working on pitch deck for education software. Yeah it’s a shitty origin story but it’s mine.

Back then you sold your entire life to some dudes for half a million bucks and gave up a lot of control. It wasn’t really collaborative but it was worth it to create the future. Back then your VCs controlled a lot more than they do now for capital they deployed. Flexibility and collaboration wasn’t really considered necessary. Your VCs actually controlled when you got fired (another childhood memory was a “take your daughter to work day” where a CEO got fired), when you could raise again, if and when you could sell your company, and honestly I wouldn’t be shocked if they had some Rumplestiltskin provisions too. That’s just where the market was at the time.

As it has become clear that non-linear returns come from creative founders and new markets, the structures of capital deployment have changed a lot. Capital cares about helping operators create because creation simply has more value than it did in the past. Venture capital isn’t old dudes optimizing for control and margin anymore (even if sometimes that might be a good idea) because that’s just not what makes money anymore.

Heck it has changed a lot in just half a decade. The last time I raised venture for my own startup, we actually priced the round (no uncapped SAFEs), we had a board from day one, and we were allowed to overshoot our valuation and capital goals by a whopping 300K. I was sure we’d reached the height of founder leverage at the time. Heck I felt certain we’d raised a small fortune on favorable & flexible terms. Six years later that would be considered a charmingly small pre-seed round with very onerous terms. Time marches on! And rightly so. Markets adapt to the needs of the participants and the returns they deliver. If it wasn’t profitable it wouldn’t be so.

This is all a long winded way of saying that I am continuing the circle of life. I’ve got my own venture fund Chaotic Capital with Alex Miller and Jacob Brody. It doesn’t look anything like the funds of my childhood or even the seed stage funds of the last decade. Probably because we as founders and operators lived through the hard lessons of venture in multiple cycles and took a lot of lessons with us. Capital isn’t about control. It’s about collaboration now. Capital starts early. Capital is flexible to generate returns But we also aren’t n00bs.

Rather than spend a year raising in silence and announcing it once it’s all said and done we are building a rolling fund. That structure works for us and my general affinity for building in public. It signals founders we are building like them (even as our other constituents see it as being responsive to the demands of the market). The rolling fund is a kind of flexibility to build at the speed of the market while also understanding that the give and take of responsible deployment must also work at the pace of founders.

While we work on forming our proper fund, we’ve created an AngelList Syndicate for chaotic where we’ll be creating SPVs for our current deals (we already have our first two which feels crazy to me) as well as follow-on deals once the fund is created. If you’re an accredited investor and interested in joining our deals, head on over. Isn’t it cool how these structures morph and change over time? I guess having a couple decades of being an operator has some benefits. You’ve seen what works and hopefully have some capacity to change what needs to be changed.

Our LPs and co-investors are mostly our friends and former colleagues who have spent years working with us at companies as varied and diverse as Stack Overflow, Trello, Easypost, Triplelift, Goop, PopSugar and over 40 different angel investments. Alex Miller, Jacob Brody and I have invested over 4m over the years which seems sort of astonishing.

While we work on forming our proper fund, we’ve created an AngelList Syndicate for chaotic where we’ll be creating SPVs for our current deals (we already have our first two!) as well as follow-on deals once the fund is created. If you’re an accredited investor and interested in joining our deals, head on over.

Categories
Emotional Work

Day 269 and Pacing

I’m very defensive of my time. While I work at curtailing reactivity in my emotional growth, it’s still easy for me to feel invaded by obligations to others. Taking video or meeting in person was among my least favorite activities even before the pandemic. That’s one reason I’ve written extensively on how to communicate with me asynchronously. But another deeper reason is my fear of misusing my time. And tempting as it may be to project it onto others, I know that this fear is entirely about me.

I am very fearful of anyone needing things from me. I don’t mean things like money, favors or advice; though it is harder to say no than you’d think. My fear is deeper. I’m afraid friends and family will start to count on me for their emotional needs when I’m still figuring out how to be present for my own. I’ll deliberately put distance between myself and others to avoid feeling needed.

So what does this have to do with pacing? I’m not very good at giving myself enough space to be challenged and recovery. And when every encounter with another person is an emotional challenge, I need to be careful about pacing myself.

Maybe there is some latent autistic spectrum issues or maybe I have more trauma than I can consciously dig up but it’s a rare human that doesn’t make me anxious about the energy required for maintaining my own boundaries. It’s not about other people to be clear. It’s about me and my fears of being emotionally invaded.

As I build up more systems and accommodations to allow me to work effectively I need to figure out better pacing. How do I connect with others without emotional fear while still respecting my needs for down time and rest? Giving myself enough recovery has been an ongoing challenge that I write about extensively. But putting it into writing also serves as a valuable reminder to course correct before a crisis emerges.

Categories
Internet Culture

Day 268 and The Game

Twitter addicts like myself love to praise the platform’s connective capacity. Sure, we might admit it’s dopamine factory that amplifies bad takes, but we’d rather focus on how it is so effective at bringing together all kinds of people and leveling the playing field of discourse. Twitter power users tend to be utopian that way. But it’s really because we’ve won the Twitter meta-game.

Twitter meta-games have been capturing the imagination in the long form discourse of Substacks and podcasts. The aggregation of influence, audience, and opinions have sorted themselves into status games that are being monetized as crypto economies and investing.

Alex Danco is the first person I saw articulate the perspective of status and world building through his Dancoland writing but recently Packy Mcormick has been furthering the discourse with his Great Online Game theory.

I wish I had a bit more capacity to go on with this topic as meta-games have been a topic I love as someone that has spent time in fashion but I find my brain and body are just coping out so I’ll remind myself that it’s alright to just capture my thoughts on the day with some links and carry on the discourse tomorrow. Save game progress. It will be here tomorrow.

Categories
Chronic Disease Emotional Work

Day 267 and Morally Neutral Accommodations

I resisted the idea of investing in a zero gravity chair. Because of my spinal condition, I find it more comfortable to work for extended periods when laying flat. Working from bed isn’t exactly ideal, emotionally or practically. And yet I wasn’t ready to sink a significant investment into my work station. Thankfully I ended my procrastination this week with the arrival of my new altwork station.

Altwork desk in a zero gravity position

It was a significant expense but I can now comfortably spend a full workday in a chair without any adverse affects. The only downside appears to be good old fashioned tiredness at the end of the day. I’m thrilled with the investment.

I wonder why I resisted the idea of investing in a comfortable desk for as long as I did. Maybe part of it was shame that I needed what felt like such an extravagant accommodation. I didn’t feel like I was worth it. Or perhaps I felt a disability isn’t something I wanted to invest in. It was something I wanted to invest in overcoming. Spending money on making my life more comfortable and functional with my disability was hard for me to swallow.

I felt if I worked hard enough at managing the symptoms of my ankylosis that perhaps eventually I’d be able to manage sitting at a regular desk for a full work day. But what kind of fools errand was I setting myself on that I desired not only discomfort but to work myself up to enduring even more discomfort? My goal was to make myself uncomfortable.

I’ve long frustrated my doctors by resisting pain management medications. I tell myself I should grin and bear it when it comes to pain. I treated pain as if it were a moral good. I suspect I was doing something similar with resisting a comfortable chair. I’ve got a problem with equating suffering with morality.

Thankfully I was able to set that aside and buy the zero gravity chair. Now rather than suffer and tell myself I’m a better person for it, I’ll actually get my work done in comfort. Which should have been the goal all along.

Categories
Chronicle

Day 266 and Out Like A Light

I nearly missed my daily commitment to write (or as it autocorrected “weird) everyday. Yesterday I was overcome by an intense need to sleep. I could barely manage to get a sentence on paper, tag it, and put it out before I passed out completely. It’s the closest I’ve ever come to missing my daily writing exercise in over two hundred days.

A narcoleptic spell would be pretty cool but I think it was a much simpler form of fatigue. I’d been so focused on a number of exciting projects (including a startup with a founder that is the best I’ve seen all year) that I just needed a rest. I couldn’t push it anymore and needed to sleep.

I didn’t feel any of the poisonous desperation from workaholic exhaustion that I’ve felt in the past. This felt like a simple tiredness that was so complete I couldn’t overcome. I fought off closing eyes as I tagged and hit publish.

And I was out. In the past fatigue has been a draining but far too lucid an experience. The kind of tiredness where you wish you could sleep but the combination of worry, focus, and anxiety would keep you awake is more familiar. I much prefer the clean tiredness of being unable to fight off sleep. Though if I need 12 hours of sleep if I work too many hours that might get a little annoying.

Categories
Chronicle

Day 265 and Sleep

I promised to weird every single day. But I cannot keep my eyes open. I want to sleep early and right now.

Maybe I wake up later but if I don’t this is enough.

Categories
Aesthetics Internet Culture

Day 264 and Shiner

I’ve been eyeing the full recline zero gravity chairs and desk combinations for a while. Because of a spinal condition sitting upright at a regular desk is tiring for me. It seemed like an extravagant purchase as they are well over $4000 at a base model but being able to spend a full work day in comfort reclining seemed worth the investment.

The Altwork chair and reclining desk

Last week I finally decided to pull the trigger and buy the chair on the advice of executive performance coach Dr. Julie Gurner who helped me see that investing in an environment that accommodates my physical needs is worthwhile.

Today was set to be the big set up and reveal day but in the excitement Alex was trying to take a picture of me laying flat while working and he dropped my phone form about three feet over my head onto my right ocular bone. It hit so hard it formed a blood bruise immediately. It was such a shock I didn’t even yell. So rather than playing with my new desk I’m icing my face.

Blood bruise from a phone hitting my face while photographing my new chair.

It hurts like hell. My face is swelling and I’ve got that jumpy nerves thing that comes from a physical trauma you didn’t see coming. So tomorrow I’ll finish setting up my new workstation. Right now I’ve got to stave off a shiner.

Categories
Emotional Work Internet Culture

Day 263 and I’m Baby

One of my friends got me an embroidered “I’m baby” patch with a Moomintroll holding a knife in place of the original Kirby. It’s an elaborate play on the “I’m Baby” meme and was a truly excellent Christmas gift. I’m a fan of the Finnish children’s author Tove Janson who created the Moomin series and also emotionally baby and my friend knows it.

Original “I’m Baby” Kirby meme vs a photo of my Moonin “I’m Baby” embroidered patch

The “I’m baby” meme is generally a play on why someone should be allowed to continue with their behavior or emotions without consequence. It’s a kind of elaborate joke about wishing to dodge responsibility if only for a few minutes. Obviously it’s very popular with Gen Z but it’s really more about wishing to live in a world where it’s even possible to be a baby when life feels overwhelming.

The original meme came out of an emergency but it’s come to be a kind of wishful demand and hope that one can just well be a baby for a bit and have someone else handle it.

Moomintroll is an excellent stand in for Kirby in the meme because in the Finnish cartoons he never has to live without Moomin Mama. Moomintroll is an archetypal baby. The Moomin universe has constant catastrophe (no seriously there are floods and asteroids) but Moomintroll can always count on Moomin Mama. It’s a soothing set of books for children obviously but it’s also just nice that there are parental figures to which one can turn. That’s a fantasy we all have at some point. Especially when shit looks bad.

But being baby also means someone else has to be the adult. The willful insistence on being baby is about giving your power to someone else. Unless you are literally baby (in which case how are you reading this blog) you’ve chosen to put someone else in the position of power. Which is an important lesson for adulthood. You always have the power. Even if you chose to be baby. Especially if you are baby.

So be careful when you say “I’m baby” and act helpless. You gave up your power. And that’s alright. Being helpless can be a totally cool sex thing and it’s great to chose your kink when. But you’ve got to have consent for that shit. Bringing someone else into your fantasy of being baby might be non-consensual. When my friend jokes that I’m baby it’s because he knows I like to give up my power. But alas it’s a fantasy and I can’t go back to being Moomintroll for real. But it’s a nice patch right?